THE PLACE: The entire top floor of Five Hundred Wellington West. The building is easily one of the most exclusive in the city; there are fewer than 20 units in total and many of them—including this penthouse—span entire floors.

BRAGGING RIGHTS: It’s the developer’s own. Peter Freed, the “man who made King West,” and the force behind this building (as well as the Thompson Hotel and Residences and other high-profile builds) bought this unit for himself, though he never ended up moving in.

BIG SELLING POINT: Like the Thompson, this condo has a great pool overlooking the city—the massive, south-facing terrace is tricked out with both a raised, infinity glass pool and a hot tub. And, unlike the Thompson, you won’t have to share them with anyone.

POSSIBLE DEAL BREAKER: You had better be able to cook under pressure—with an open, restaurant-style kitchen, dinner guests will be watching your every move.

The penthouse unit takes up the entire top floor. It is separated into living and entertainment areas, each with its own private elevator. The living space has a wood-burning fireplace set into a marble feature wall